Third Time's a Charm
by So Much Tea
Summary: Killian Jones is struggling finding the courage to ask Emma Swan out to dinner. He's a pirate, for goodness sake! Why is it so difficult? That is until he comes across a time pod, something that will allow him to ask Emma out again and again and again until he can get it right. Captain Swan.


Third Time's a Charm

* * *

 **This was a prompt I had on Tumblr and I had SO MUCH fun writing this! Seriously. I hope you guys enjoy!**

* * *

Captain Hook was not afraid of anything.

He had faced beasts beyond imagination, pierced their scaly grey skin and slimy green tentacles until they'd fallen at his feet. He'd sailed through storms where waves towered to the top of his masts, and spray made it almost impossible to see. He had felt the icy chill of the sea air. He had killed a man. He had killed many men, good and bad. Not many things could turn his stomach after seeing his own severed hand on the deck below him.

Killian Jones, however, was an entirely different matter altogether.

 _Just ask her out,_ he told himself. What was the worst that could happen? And isn't that what modern people did - asked out those who caught their attention? It was much simpler than the ways in his own realm. Usually a lengthy courting would take place. Or, if one was a pirate, a drink and a good old shag in the Captain's quarters would do it.

But he suspected Emma Swan would want to be treated properly. And she deserved it. God knows, she deserved it. If he had his way, he'd treat her like the princess she was. He wouldn't mind courting her at all, even if it took months. Years, even. As long as she was his in the end.

But according to a good old book he'd borrowed from the library so named, "How to pick up that chick you really want", courting wasn't the style anymore. Dinners were deemed more more appropriate.

According to the book, he'd done everything all wrong. Dinners always came before kissing. Yet, he and Emma had shared a brief but passionate kiss in Neverland when they were trying to save her boy. It was true that he hasn't instigated the kiss, but he still should have put a stop to it. He should have pushed her away with his hand and hook (gently, of course) and insisted they begin the courting period immediately.

The only thing was, he couldn't exactly work up the courage to ask Emma out to dinner.

He'd had many chances of course. He saw her all the time, either chasing after some sort of monster with her faithful crew behind her, or on her own, running errands. He often caught her in Granny's. He'd open the door to the delectable scent of coffee and doughnuts, basking in the wave of warmth the place admitted. But then he'd spot her. She was always sat at the bar with her back to him, her ruby leather jacket stretching around the curves of her body. Her golden hair falling in soft waves around her shoulders. She'd flip it behind her, so casually, and it would stun him.

And then he'd run for it.

Now, Captain Hook had never run away from anything. Not _anything._ But Emma Swan could send Killian dancing all the way across Storybrooke.

That was until he'd think of her again. Missing her would come in waves, then stronger, and soon missing her was like a storm he couldn't best. He'd find himself thinking about her smile, and the curves of her cheeks and the light in her eyes. He'd just want to hold her and protect her.

Not that Swan needed protecting.

One particularly frosty Sunday morning he'd ran all the way back to his ship. He threw himself up the stairs to the deck, collapsing on one of the wooden crates, letting himself deflate. He was sweating, the leather sticking to him. He shredded off his coat and wiped his forehead.

God, she was going to be the death of him.

"Running from the Swan girl again, Captain?"

Killian gave a start, almost falling off his wooden box. His heart beat wildly in his chest. He drew his sword and slashed it in the air. Smee ducked to avoid the fatal blow that would deem him headless.

"You!" he yelled when he saw who it was. "What do you think you're doing, bloody sneaking up on me?"

"Not sneaking up, Captain, never sneaking up," said Smee, removing his red hat, mopping his forehead with it. He turned it in his hands. "Just scrubbing the deck, as you asked me to do this morning."

"Get to it, then!"

"Certainly. But uh… Captain?"

Killian glanced over at his second in command. Smee looked more nervous than usual. Ever since Killian had found a way to turn him back into a human after Gold magicked him into a rat, he'd been more twitchy than ever. Killian noticed he never killed the rats he found on deck anymore. He let them scurry free.

"Think carefully about what you're going to say." The warning in his voice was enough to make anyone quiver. He had to admire Smee's bravery.

"Of course. Yes. Always." He swallowed and nodded, still twisting that hat in his hands, twisting until it became a deformed lump. "It's just… I think I may have a way to help you."

Killian's gaze snapped to his. "Help me?" he asked, sharply. "How could _you_ possibly help _me_?"

"With the- with the Swan girl, Captain."

Killian couldn't help it, his face flamed. He'd never been particularly careful when it came to Emma, but he hadn't expected Smee to say anything. Smee should have learned after all those years together that the Captain could do many things and be sure the crew wouldn't speak of them.

There was only one thing Killian could do now. Deny, deny, deny!

"I have no idea what you're talking about. I don't need your help."

"Of course." Smee ducked his head. "But Captain, I really think this could help."

Killian sighed. Was Emma really such a hopeless case that his own crew were offering their assistance? As stupid as Smee was, perhaps he did have something that could help. He'd been useful over the years. And he seemed determined that Killian should hear what he had to say.

"Right then," he sighed. "Out with it."

Smee drew in a breath, averting his eyes to the wooden deck. "Well, I couldn't help but notice the book in your cabin. The book about women." He cowered under the look Killian gave him. "And- and I don't think it's very helpful, Captain. But I- I have something that might help. It's a time pod-"

"A what?"

"A time pod, Captain. I found it in the Dark One's office."

"You've been in the crocodile's office?" Killian didn't think he had it in him. The crocodile was dangerous at the best of times, let alone when people tried to steal his things.

"Aye, Captain. I noticed you haven't really been yourself, so I just wanted to help you. I knew that the Dark One _must_ have something. And then I found this time pod left out over an open book. The book said it can help you go back in time."

Killian froze. "Go back in time? How would that help me?"

"You can only go back for a few hours at a time. It works like a magic bean. You throw it and you get a portal, but it doesn't go away. You pick it back up and you can use it again and again. I just thought-" He paused, colour rising to his cheeks. "You could use it. Court the Swan girl. And if it doesn't go to plan, or if she doesn't return your affections…"

"I can go back in time and pretend it never happened," he murmured.

He'd never have to go through the embarrassment and humiliation of being turned down by her. He could try and if it should fail, he could go back in time and Emma wouldn't have to know a thing. It was brilliant. Ingenious.

He accepted the time pod from Smee almost gleefully and shoved it in his coat pocket, which he'd left strewn across the deck. He was going to do it. He was going to win the affections of Emma.

After he bathed, of course.

* * *

A few hours later he stood outside the door of the Charmings' residence, smelling as fresh as a daisy. Though he'd washed and combed his hair, it stuck to his forehead and the back of his neck, where he felt the hottest. If he were honest with himself, he felt hot all over.

And his _heart._ After Milah died, he had to question whether he still had one. But God, how it raced, like it was trying to jump out of his chest. He could feel it in his ears and his neck. The relentless beat filled his head. He wiped his hands on his leather coat but they slipped off as easily as if he'd coated his hands in butter.

Bloody hell, he was a mess.

And she was a Goddess.

He was just about to turn and run again when the door swung open. It was Emma - and it _would_ be, wouldn't it - eyes widening slightly in surprise. Her eyes were so beautiful, with flecks of green and yellow. He could spend hours gazing into them.

"Oh. It's you," she said. "What do you want?"

The indifference in her voice gave him cause to turn around. But he didn't. He leaned against the doorway, assuming the position of smooth pirate, and looked at her through hooded eyes. The hooded eyes always worked on women. That was, if the leaning hadn't already entranced them.

"Swan," he said. "I must say, you look divine." Did she notice the slight tremble in his voice?

"Hook. Tell me what you want and make it quick. I'm busy."

That was it. The moment. All he had to do was get the words past his lips, even though his tongue felt thick in his mouth and her perfume was _intoxicating_ him. He had the strange, overwhelming desire to pull her close and kiss her into an oblivion, like he had in Neverland. Or had _she_ kissed _him_ into an oblivion?

Perhaps doing so would have been a smarter move than what he actually did.

"Well, love, I was wondering if you were free - and by free, I mean available - I think that's what you modern people call it, available, in the sense that you're doing absolutely nothing and by absolutely nothing, I mean-

Her eyes widened, just a touch, and then she narrowed them. "Just spit it out."

"I was simply thinking that perhaps, if you are indeed available that perhaps we could spend a night together-"

Her eyebrows flew up. "A night together?"

Oh, _shit._

"Not in that sense!" he rushed out. "Though you are very beautiful, _very very beautiful_ and a night with you- well, darling, let's just say I wouldn't forget it in a hurry. And I have been with plenty of wenches-"

" _Wenches_?" she asked, voice sharp.

His eyes widened. "Bloody hell. I'm not implying you're a wench."

She folded her arms and leant against the doorframe herself so she was inches from him, lips curling into a smirk. Was she mocking him? "What _are_ you implying?"

"I'm not implying anything. I'm just trying to- I'm trying-"

 _Just say the words_ , he screamed at himself. How hard was it? He'd faced krakens and dragons and yet, here he was. Emma Swan had managed to turn him into a stuttering, blushing mess in a matter of seconds, and she hadn't even done anything.

"Are you trying to ask me out?" Her tone was nonchalant, though her eyes were mysterious and that smirk was still playing around those gorgeous lips of hers.

She was _definitely_ making fun of him. Back when he was a pirate, he would have took her head off for that. Instead, he had to fight the urge to kiss the smirk away.

"No!" he all but shouted. "Yes. Bloody hell. Goodbye."

He turned and bolted down the stairs, leather coat swishing behind him. He heard her call his name, but he ignored her, jumping down the stairs three at a time.

Only when he was outside, could he breathe again. He gulped in generous amounts of fresh air, thankful for the breeze. It cooled his forehead and his neck. He could think clearly without that flowery smell penetrating his nose and turning his head to mush.

That couldn't have gone any worse. He couldn't have messed it up any more than he had. It would have been fine if he'd simply asked her out, and she turned him down. He could live with that. But he'd humiliated himself completely and utterly.

Captain Hook, a name which once struck fear into the hearts of men and women, a bumbling buffoon.

He was on his way back to his ship, red faced and ashamed, when he remembered the time pod. He slipped his hand into his pocket and pulled it out. It was bigger than a bean, more like the size of a peach stone, though it was a vibrant red.

 _What harm could it do,_ he asked himself. He could throw the pod down, disappear into the past, and try again. No-one would have to know. Not Emma or the rest of the heroes, who would probably try and stop him if they knew what he was about to do. Even he knew messing with time could be dangerous.

But all for a good cause…

Before he could change his mind, Killian threw the pod down onto the ground. A purple whirl appeared in the middle of the dusty pavement, full of stars and light. _Here goes it_ , he thought and jumped down into the darkness.

After the sensation of being pulled through a tight rubber tube, Killian hit the same spot he jumped from, gasping for breath, palms scraping against the concrete. He already knew it was a few hours earlier. The ground was wet from a fresh shower of rain, the scent of mud filling his nose.

The portal disappeared, leaving the pod in its place. Gathering his bearings, Killian jumped to his feet and swiped dust from his leather coat. He was amazed. He wasn't sure if it would actually work, being property of the crocodile, yet there he was. It must be his lucky day, he thought as he scooped the pod from the pavement and dropped it back into his pocket.

It was time to woo Emma, far more successfully than he'd done a few moments ago.

He climbed up the chipped stairs to Emma's flat a second time. He was so elated from his journey through time, he didn't even stop to consider what he was doing. Instead, he rapped his hook against the wood. The door opened almost immediately.

She looked exactly the same as she had a few moments ago, her hair cascading down over the cream jumper she wore. He had to stop himself from leaning in when he caught a whiff of her perfume again.

"Huh, it's you," she said. "What do you want?"

He found himself frozen again. Why? _Why?_ What had this woman done to him? Was she some sort of enchantress, able to bewitch him with every movement? No-one had affected him like this, not even Milah, whom he had shared years of his life with.

"Hook?" she asked, raising a perfectly arched brow. "I haven't got all day."

"I WISH TO COURT YOU." He didn't realise he'd shouted the words until they'd escaped his lips and by that time, it was too late.

With one last panicked look thrown in her direction, he found himself running down the stairs again.

"Hook!" she called. "Hook, wait!"

When he got outside, he didn't even consider it, he just threw the pod down onto the ground and jumped into the portal. Going back a few more hours wouldn't do serious harm.

He made his way back to her flat again, but it was her same-age mother, Snow White come Mary Margaret, who answered. She told him that Emma was probably at Granny's, getting her usual lunch of coffee and grilled cheese, whatever that was. He shuffled under her gaze, which seemed a little _too_ understanding. When she offered to "call" Emma, and pulled a rectangle box-like thing from her pocket, he slowly backed away. When it started beeping rudely, he told her he'd just check Granny's and if she wasn't there, he'd call it a day.

As it turned out, she _was_ at Granny's, though she was just leaving. He caught her in the doorway, holding a paper bag in one hand and a coffee in the other.

"Hook," she greeted, with a nod of her head.

And then she did something he hadn't seen in so long. Something that made his heart ache and his stomach flip. She smiled at him. Genuinely smiled at him. God, if it wasn't the most beautiful thing he'd ever witnessed, he didn't know what was.

So he took her by her shoulders and pressed his mouth to hers. Her lips were soft, just like they had been in Nerverland, and her perfume was even stronger when he was this close. He had all of two seconds to bask in the feeling before she pushed him off her.

He expected to see a look of true love (or, more realistically, uncontrollable lust) but instead she looked- she looked-

Well, she looked pissed off, to say the least.

"What the _hell_ was that?" she yelled at him. Her hair whipped around her face, which was lined with anger. He'd never seen her forehead pucker like that.

Without hesitation, he disappeared through the portal.

* * *

It continued much like that.

He'd either kiss her, and she'd push him away and shout (in some cases, obscene curses) at him, or he'd try and ask her to dinner, but he'd mess up his words. Sometimes he'd accidentally call her a wench again, or a slag, or another thing which didn't mean the same in Storybrooke as it did in the Enchanted Forest.

So he knew it was time to come up with a different plan.

He didn't need to be Killian. He needed to be _Hook._ Instead of kissing her outright, he needed to make her want to kiss him. And if there was anything he was truly talented at, it was the art of seduction.

The next time he made his way to her flat, he'd stepped into his alter ego. Killian Jones was abandoned at the bottom of the stairs. Killian wouldn't mess it up for him this time. Hook would prevail.

She was alone that time. The Charmings had taken Henry out to the park for ice cream. He asked Emma if he could come in, because he had something incredibly important to discuss with her. To his utter amazement, she disappeared into her home, leaving the door wide open.

He sauntered into the room.

"So, what's so important you had to come all the way here for?" she asked, as she made her way into the middle of the room. She turned to face him, arms folded.

He closed the door behind him. "I'm not sure you could handle it," he said slowly, looking at her through his hooded eyes.

She froze. "Huh."

He took a slow step towards her. "It's a… delicate situation." Then another. And another. And another until he was only inches away from her. She didn't move but became incredibly still, looking up at him. The light cast shadows under her eyelashes. He'd never noticed how incredibly long they were. "I want to talk."

"Talk?"

"About us."

"There is no us," she said at once, but she averted her eyes to the floor.

"Oh Emma," he began, lowering his voice just right. He found if he could get it at the right octave, it would become as smooth as honey. He'd used it on her at the beanstalk, to see if she'd flirt back with him, as many women have. Of course, she didn't. But that was then. She didn't even _know_ him back then. This was now. "You can't deny that we have a connection."

"We don't have-" But her voice faltered. She swallowed. Then, hardly a whisper, "A connection."

He'd never seen her like that before. Usually she looked him straight in the eyes, feet planted firmly on the floor, arms crossed. But the way she moved her eyes away from his was almost shy. He knew he was treading dangerous water, but he had to know. He had to try.

"Emma," he murmured. " _Darling_ ," he purred. _That_ made her blush. He'd never seen her blush before, not even when she spoke about being in love that one time. His stomach did that weird flippy thing again. He fought to remain composed. "I admit, I have been quite immoral-"

"A villain."

"- in the past. But I believe that I can change."

" _I_ don't believe you can change." But her voice was soft, almost pleading.

"Is that why you're going to let me kiss you?"

"I'm not going to let you kiss me," she scoffed.

He pressed his lips gently to hers. This time instead of taking her by the shoulders, he took her into his arms, holding her with the softest of touches, as if she might break. She seemed to melt as he kissed her softly, tenderly.

It was everything he imagined it would be and so much more. It was embarrassing how many times he'd imagined this moment, how many times he'd played it over and over in his head. When he brought his hand up to her head, her hair was softer than he'd ever thought it would be. He hadn't really took in the softness of her hair during their intimate moment in Neverland.

Neverland wasn't like this. Neverland was passionate and quick. This was slow and sweet.

And the soft noise that she made when he pulled her closer still. God, he could get used to this. He'd never heard anything like that from her before, but he might die if he never heard it again. Yes! God bless Smee and that pod. He'd never say another bad thing about Smee again.

BANG.

The door flew open.

They jumped apart. Killian felt her leave like she'd been ripped from him. Embarrassingly, he reached for her but she was halfway across the room, not looking at him.

David stood in the doorway, his expression murderous.

"PIRATE," he yelled.

Killian was already pulling the pod from his pocket.

* * *

"Have you ever been kissed by a pirate before?" Killian asked between feverish kisses.

"No," Emma murmured against his lips. Her hands were in his hair, her fingers dragged along his head, making him feel like he was losing his mind. "But I thought you were-" Kiss. "-not real-" Kiss. "-a fairytale."

"I assure you darling, I am very much real. Would you like me to prove it?"

"If you think- _Oh God,_ " she gasped when he gently bit a particularly sensitive spot on her neck.

He couldn't believe his luck. He'd been worrying about how he could ask her out and yet there she was, liquefying in his arms as he'd imagined so many times. He only _dreamed_ he could have this effect on her. Yet, she seemed to respond to his every touch. It was a bloody miracle.

They shifted so they were lying down on the sofa, her hands still in his hair.

"How long have you felt this way?"

"Kiss now, talk later," she rushed out. He pressed a kiss to her throat. He could do that forever; press kisses to her skin and wait for her to respond to them. It was the most glorious-

BANG.

"PIRATE."

…

Killian knocked on the door a little too desperately and breathlessly, but _God_ , he needed to get back to that place where she was under him and she was whispering things he never thought he'd hear her whisper.

"Hook?" she asked, when she opened the door.

"Use my God-given name."

The look on her face was enough to find that pod again.

* * *

"This is just- it's, uh-" He chuckled nervously, shaking his head. "I apologise for my stunted words, it's just that I've never… done this before." That much was true. He'd never asked Milah out. She'd practically begged him to come away on his ship.

He scratched the back of his head. "I just think you're the most beautiful creature I have ever seen. I have never been so entranced in all my life. I am unaware of what spell you've cast over me, but I'm not sure I want it to end. I know that perhaps this may seem all too sudden, which is why I propose we go slow. I shall go at your pace. You cannot deny that we have a connection."

Silence.

"Come on, love. It's bad form to make a man wait like this. Please. Say something."

David stepped into view, wearing a very confused expression on his face.

"I'm, uh, sorry Hook, but I'm a married man! And you're- well, a pirate."

 _Bloody hell._

* * *

The next time Killian made _sure_ that he wouldn't run into David. He avoided him at all costs. He actually liked his head where it was, and he wouldn't be surprised if David took it clean off. _Thank God for the pod,_ he thought as he skipped back up the stairs to Emma's apartment. At least David wouldn't remember their conversations, even if Killian knew _he'd_ never forget them.

But he didn't run into David. Or Emma, for that matter.

It was Mary Margaret who answered. She looked at him with her eyebrows raised, and it was _so_ like Emma, he felt his heart pick up at the image. Or perhaps his heart was picking up because he knew she wasn't _too_ taken with him.

Alas, he couldn't blame her. He was still struggling the whole villain-hero thing. Perhaps there was a group for that.

"Emma's not here," she said, with a small smile.

"Oh," he said. "Right. I see." He nodded.

"Why do I feel like we've done this before?" she asked with a thoughtful head tilt.

"We haven't!" he said too quickly.

The time pod felt heavy in his pocket. He expected it to jump out and reveal him. Magic had always seemed alive somehow, like it had a mind of its own. Afterall, didn't magic always come with a price? He wondered what his price was.

"Should I give her a message for you?"

"No, love. I suppose I'll just find her." He scratched behind his head. "Thank you anyway."

He turned, his coat flapping behind him in the self-made breeze. He'd only just reached the top of the stairs when-

"Keep trying, Hook."

He turned, forehead crinkling. "Sorry, what?"

"With Emma," she said. Then she lowered her voice. "She's not the type of person to kiss someone on a whim. Not someone she _knows_ , at least. I think… something's there. I'm not sure what, but there's something. Between both of you, I mean."

"I don't know what you're talking-"

"Oh, I think you do," she said, with a sparkle in her eyes. "And… you're not a villain anymore. Are you?"

"I-" He looked away, abashed. "I suppose I-" He shakes his head. "I've always been a Pirate."

"We'll see."

Without any further explanation or comment, she closed the door. Hook was left to stand there, looking around, not really sure he believed his ears. Was this because he saved the prince's life? Perhaps being a hero really did have it's perks.

* * *

He found Emma stood outside Granny's, a coffee in her gloved hands. She looked as beautiful as ever, with her hair rippling gently in the breeze. Her leather jacket was zipped up to her throat. She flipped her hair over her shoulder and surveyed the street around her with a calculating expression. His heart fluttered in his chest.

This time, he knew what he was going to say to her.

He was going to be honest with her. And if she said no, he was going to tell her he would fight for her. Until his dying breath.

He started walking towards her.

Henry got there first. She smiled and draped her arm around his shoulders, pulling him closer to her. Killian would have kept walking -afterall, he liked the boy- if it wasn't for Baelfire. He seemed to come out of nowhere, walking straight for Emma. Her face lit up when she saw him.

The expression, which would have usually made him smile, pierced him. It was like he'd had the breath knocked out of him.

It was all too like that damn cave in Neverland. He had felt happy that Baelfire wasn't dead. After what happened between them when he was a boy, he couldn't deny he owed him something. Anything. And yet…

And yet, the selfish part of him ached to see his return. The way his arms curled around Emma in that cave, how he held her close and how she hugged him like she'd never be able to breathe if she let go. She had never held Killian like that.

Hell, she hadn't even _held_ Killian. She'd never smiled at him like she smiled at Baelfire. Watching them walk off together, he knew where her true affections laid.

Feeling ashamed, he drew the pod from his pocket. He held it in the palm of his hand for a moment. It was almost like he could feel its heart ticking away. Or was that his? He didn't know. All he knew was that the pod was dangerous. It had to go.

With a heavy sigh, he threw it into the pavement. He watched as it bounced and rolled, eventually tumbling down the drain.

There. Now he would never be tempted to go after Emma again. He'd never be tempted to get back into that cycle of asking her to be his over and over and over. Not when he knew she was happy elsewhere.

Perhaps that was the price. Perhaps it was for the best.

Shaking his head, he turned around and headed back to his ship.

* * *

It wasn't until years later, after the time portal, after Camelot and after the Underworld, when Emma was lying so soft and sweet in his arms, that Killian recounted the time pod and his antics to win her affections. He stroked his fingertips down her back, murmuring into her hair that when he saw her with Neal, he just ran.

He would never be worthy.

Of course, Emma told him that he was stupid. Of _course_ he was worthy. Look at everything he'd done for her! Look at everything she'd done for him. They were worthy of each other. He'd suspected she'd say that.

But what he didn't expect was her telling him that if he asked her out to dinner, as he'd planned, simple and plain, she would have said yes. She might have cancelled a few times, screamed at herself that he was a _Pirate_ , but she would have said yes. Because deep in her heart of hearts, she knew.

Satisfied with that answer, Killian pulled her close.


End file.
